Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 9 (September 2012)

organic compounds

Hydrogen bonding in cyclic imides and amide carb­oxy­lic acid derivatives from the facile reaction of cis-cyclo­hexane-1,2-carb­oxy­lic anhydride with o- and p-anisidine and m- and p-amino­benzoic acids

Abstract: The structures of the open-chain amide carb­oxy­lic acid rac-cis-2-[(2-meth­oxy­phen­yl)carbamo­yl]cyclo­hexane-1-carb­oxy­lic acid, C15H19NO4, (I), and the cyclic imides rac-cis-2-(4-meth­oxy­phen­yl)-3a,4,5,6,7,7a-hexa­hydro­isoindole-1,3-dione, C15H17NO3, (II), chiral cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C15H15NO4, (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid monohydrate, C15H15NO4·H2O, (IV), are reported. In the amide acid (I), the phenyl­carbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) Å for the amide O atom] and the mol­ecules form discrete centrosymmetric dimers through inter­molecular cyclic carbox­y-carboxy O-HO hydrogen-bonding inter­actions [graph-set notation R22(8)]. The cyclic imides (II)-(IV) are conformationally similar, with comparable benzene ring rotations about the imide N-Car bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak inter­molecular C-HOimide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong inter­molecular carb­oxy­lic acid O-HO hydrogen-bonding associations. With (III), these involve imide O-atom acceptors, giving one-dimensional zigzag chains [graph-set C(9)], while with the monohydrate (IV), the hydrogen bond involves the partially disordered water mol­ecule which also bridges mol­ecules through both imide and carboxy O-atom acceptors in a cyclic R44(12) association, giving a two-dimensional sheet structure. The structures reported here expand the structural database for compounds of this series formed from the facile reaction of cis-cyclo­hexane-1,2-dicarb­oxy­lic anhydride with substituted anilines, in which there is a much larger incidence of cyclic imides compared to amide carb­oxy­lic acids.

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